HCID 15612343, compound → (+/-)-alpha-amino-alpha-methyl-N-(2-phenylethyl)-1H-indole-3-propanamide

HRID 1781193Notes

Reaction equation

HRID 1781193 reaction equation
C1C2C(COC(=O)[NH:17][C:18]([CH2:31][C:32]3[C:40]4[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=4)[NH:34][CH:33]=3)([CH3:30])[C:19](=[O:29])[NH:20][CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)C3C(=CC=CC=3)C=2C=CC=1>N1CCCCC1.CN(C=O)C>[NH2:17][C:18]([CH3:30])([CH2:31][C:32]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[NH:34][CH:33]=1)[C:19]([NH:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:29]

Participants

4

Reactant 1

HCID 15612343HCID 15612343, compound

Product 1

HCID 14560809(+/-)-alpha-amino-alpha-methyl-N-(2-phenylethyl)-1H-indole-3-propanamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8082PiperidineSolvent

Procedure

(±)-9H-Fluoren-9-ylmethyl[1-(1H-indol-3-yl-methyl)-1-methyl-2-oxo-2-[(2-phenylethyl)amino]ethyl]carbamate (10 g, 18.4 mmol) was dissolved in a 20% piperidine in DMF solution (50 mL) and stirred for 12 hours at room temperature. The solvent was removed in vacuo and chromatographed over silica gel using CH2Cl2 then 5% MeOH:95% CH2Cl2 as eluants. The title compound was crystallized from ethyl acetate (4.73 g, 80%), mp 106°-110° C. (EtOAc); IR (film) 1646 cm-1 ; NMR (CDCl3) δ1.39 (3H, s), 2.56-2.74 (2H, m), 2.82 (1H, d, J 14 Hz), 3.28-3.40 (1H, m), 3.48 (1H, d, J 14 Hz), 3.44-3.53 (1H, m), 7.1-7.7 (11H, m), 8.3 (1H, s); Anal. (C20H23N3O) C, H, N.

Workup

  1. customThe solvent was removed in vacuo
  2. customchromatographed over silica gel
  3. customThe title compound was crystallized from ethyl acetate (4.73 g, 80%), mp 106°-110° C. (EtOAc)

Sources & evidence

ORD record
ord-6f4a8f6f927b494c8555f6160b05f82a
Source dataset
uspto-grants-1997_05
Patent number
US05631281

Reaction notes

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